title: Synthesis of thiophene 1,1-dioxides and tuning their optoelectronic properties.
abstract: A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1-dioxide were utilized in a series of Stille cross-coupling reactions to afford thiophene 1,1-dioxides with either electron-donating or electron-withdrawing substituents. Electron-withdrawing groups greatly facilitate the reduction of these sulfone heterocycles, and -C6H4-p-NO2 substituents produce a 510 mV shift as compared to a thiophene 1,1-dioxide with two phenyl groups.
authors.affiliation: Department of Chemistry, Carnegie Mellon University , 4400 Fifth Avenue, Pittsburgh , Pennsylvania, 15213, United States.
authors.forename: Chia-Hua
authors.initials: CH
authors.lastname: Tsai
authors.forename: Danielle N
authors.initials: DN
authors.lastname: Chirdon
authors.forename: Andrew B
authors.initials: AB
authors.lastname: Maurer
authors.forename: Stefan
authors.initials: S
authors.lastname: Bernhard
authors.forename: Kevin J T
authors.initials: KJ
authors.lastname: Noonan
mesh_terms: D055664:Electrochemical Techniques; D015394:Molecular Structure; D009947:Organotin Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C587562:2,5-bis(tributylstannyl)thiophene 1,1-dioxide; D009947:Organotin Compounds; D013876:Thiophenes